Reaction of diazonium salts with transition metals—III

Kikukawa, Kiyoshi; Nagira, Kazuhiko; Wada, Fumio; Matsuda, Tsutomu

doi:10.1016/s0040-4020(01)97711-7

Cited by 151 publications

(59 citation statements)

References 13 publications

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“…The use of trifluoroacetate salts led to a reduction in the reaction times at radical chain reactions. Indeed, attempts to use phosphane coordinated to transition metal ions (Rh II , Pd II , Pd 0 ) failed room temperature compared to those with tetrafluoroborates, [47,50,54] thereby rendering the coupling reactions much to give any coupling products, but essentially only hydrodediazoniation products instead. Consequently, even though faster than any spontaneous dediazoniation.…”

Section: Quinone Diazidesmentioning

confidence: 99%

An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications

Colas

Goeldner²

1999

Eur. J. Org. Chem.

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We have developed a very mild procedure for the synthesis of crystalline aryldiazonium trifluoroacetate salts in high yields under anhydrous conditions. Over thirty mono‐ or polyfunctional aniline derivatives have been diazotized by this method, including water‐ and acid‐sensitive substrates. The o‐ and p‐hydroxyaryldiazonium salts, derived from the corresponding anilines, could be deprotonated by treatment with K2CO3 to yield pure diazoquinones. NMR and UV/Vis spectra have been recorded for all the synthesized salts; the data are in good agreement with the rather limited published data and constitute a first extensive report of 13C‐NMR chemical shifts in diazonium salts. An excellent linear relationship emerged between Brown's substituent constants s+p and the 13Cipso chemical shifts. The diazonium salts obtained proved to be much more soluble in organic solvents than their tetrafluoroborate counterparts. They were tested in Pd‐mediated coupling reactions of various Carbon‐Carbon double bonds, and were found to give good yields within short reaction times under very mild conditions. We believe that diazonium trifluoroacetates represent a very attractive alternative to diazonium tetrafluoroborates.

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Section: Quinone Diazidesmentioning

confidence: 99%

An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications

Colas

Goeldner²

1999

Eur. J. Org. Chem.

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“…[18] Since these starting materials are sometimes quite expensive and/or a particular substrate not easily accessible, we started to look for alternative substrates. At about the same time, Matsuda and coworkers [19] described an effective olefin arylation reaction with aryldiazonium salts, easily accessible by diazotation of the corresponding anilines, i.e., ubiquitous and cheap starting materials. In 1982 we reported that aroyl chlorides were also suitable coupling components with a reactivity similar to aryl bromides (see Figure 3).…”

Section: New Substrates For Heck-type Arylation Reactionsmentioning

confidence: 99%

“…At the same time as the just published Pd-catalyzed reaction of olefins with aryldiazonium salts [19] (a variant of the Heck [18] reaction) was investigated at the Central Research Laboratories of Ciba-Geigy, its Agro Research Department was interested in new sulfonylurea herbicides (see Figure 15). When the involved chemists realized that a variety of o-substituted benzenesulfonic acids would be accessible via this methodology, about 30 different derivatives were prepared.…”

Section: Building Block For a New Herbicide Via Thementioning

confidence: 99%

Industrial R&D on Catalytic CC and CN Coupling Reactions: A Personal Account on Goals, Approaches and Results

Blaser¹,

Indolese²,

Naud³

et al. 2004

Adv Synth Catal

216

103

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R&D issues for the application of Pd-and Ni-catalyzed C À C and C À N coupling reactions in the fine chemicals industry are discussed. In a first part, some background is given on industrial R&D and the role of C À C and C À N coupling for preparative applications is described. The following principal approaches to industrial research are illustrated with relevant examples from the literature and from our own laboratories: i) development of catalysts and catalytic methodologies with industrial potential; ii) finding shorter routes to target molecules using catalytic methods; iii) development of industrial catalytic processes in multi-step syntheses.

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“…Additionally, the reaction can be performed with or without a base and is often faster than traditional Heck protocols. 7 Our attention was drawn to the work of Hyde and Buchwald 8 in which it was disclosed that β,γ-unsaturated lactones such as α-angelicalactone could be selectivity coupled with aryl halides at the γ-position (Scheme 1). Although a typical Heck procedure employing Pd(OAc) 2 and a monodentate phosphine as catalyst was employed, an unusual combination of toluene and t-amyl alcohol as solvent was critical to the success of the reaction.…”

Section: Introductionmentioning

confidence: 99%

Arylation of β,γ-unsaturated lactones by a Heck-Matsuda reaction: an unexpected route to aryldiazene butenolides and pyridazinones

Taylor¹,

Correia²

2010

Quím. Nova

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Recebido em 15/6/10; aceito em 6/8/10; publicado na web em 18/10/10The palladium catalysed coupling of aryldiazonium salts with β-γ-unsaturated lactones under basic conditions has been investigated. Both (3H)-furanone and α-angelicalactone were evaluated as substrates in the Heck Matsuda reaction but both failed to afford the desired arylated butenolides. Under basic conditions, β-γ-unsaturated lactones generate highly nucleophilic enolates that preferentially undergo azo coupling reactions with arenediazonium salts to afford aryldiazene butenolides. The electronic and steric effect of the substituents on the aryldiazonium salt in the azo coupling reaction is described. Aryldiazene-lactone derivatives were obtained in good yields from a highly facile and straightforward procedure. An aminoisomaleimide was formed from (3H)-furanone and cyclised to the corresponding pyridazinones in modest yield.

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Reaction of diazonium salts with transition metals—III

Cited by 151 publications

References 13 publications

An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications

An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications

Industrial R&D on Catalytic CC and CN Coupling Reactions: A Personal Account on Goals, Approaches and Results

Arylation of β,γ-unsaturated lactones by a Heck-Matsuda reaction: an unexpected route to aryldiazene butenolides and pyridazinones

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